Water → 4-(2-(2,6-Dimethyl-3-nitrophenoxy)pyridin-3-yl)pyrimidine

HRID 1361686

Reaction equation

HRID 1361686 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[C:3]=1[OH:12].Cl[C:14]1[C:19]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][N:21]=2)=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[C:3]=1[O:12][C:14]1[C:19]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][N:21]=2)=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 814763-Nitro-2,6-xylenolHCID 161089744-(2-Chloropyridin-3-yl)pyrimidine

Product 1

HCID 669706854-(2-(2,6-Dimethyl-3-nitrophenoxy)pyridin-3-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolved 2,6-dimethyl-3-nitrophenol (1.96 g, 11.7 mmol) and 4-(2-chloropyridin-3-yl)pyrimidine (1.50 g, 7.83 mmol) in dimethylsulfoxide (15.0 ml) and added cesium carbonate (5.10 g, 15.7 mmol). Reaction mixture was heated to 1200C in a sealed tube for 8 hours. Reaction mixture was then allowed to cool to room temperature and then poured into 250 mL of rapidly stirring water in an Erlenmeyer flask. After 10 minutes, the opaque brown aqueous solution was cooled to 0° C. and allowed to stand for 10 minutes, then filtered. The precipitate was collected as the title compound. MS m/z=323 (M+H)+. Calc'd for C17H16N4O3: 324.34.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperaturethe opaque brown aqueous solution was cooled to 0° C.
  4. waitto stand for 10 minutes
  5. filtrationfiltered
  6. customThe precipitate was collected as the title compound

Sources & evidence

ORD record
ord-9896c3dafcf04df5a1785cc19e976847
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Linked notes

Loading…